Triethylamine → 2-(3-Methoxyphenyl)-2-propanamine

HRID 2071052Notes

Reaction equation

HRID 2071052 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:14])(C)[C:10](O)=O)[CH:6]=[CH:7][CH:8]=1.C([N:17](CC)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1>CC(O)(C)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([NH2:17])([CH3:14])[CH3:10])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 108216342-(3-Methoxyphenyl)-2-methylpropanoic acid

Product 1

HCID 139113102-(3-Methoxyphenyl)-2-propanamine

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To 2-(3-methoxyphenyl)-2-methylpropanoic acid (330 mg, 1.70 mmol) and triethylamine (191 mg, 1.87 mmol) in t-BuOH (15 ml), DPPA (514 mg, 1.87 mmol) was added and the resultant solution was refluxed for 2 h. Then t-BuOH was removed under vacuum. Crude residue was dissolved in THF (10 ml) and 2N HCl (10 ml) was added and stirred overnight at RT. Then solvent was removed, crude residue dissolved in water and extracted with ether. Aqueous layer was basified with 5N NaOH and extracted with ethyl acetate. Organic layer was dried and evaporated to yield 2-(3-methoxyphenyl)propan-2-amine.

Workup

  1. customThen t-BuOH was removed under vacuum
  2. dissolutionCrude residue was dissolved in THF (10 ml)
  3. addition2N HCl (10 ml) was added
  4. customThen solvent was removed
  5. dissolutioncrude residue dissolved in water
  6. extractionextracted with ether
  7. extractionextracted with ethyl acetate
  8. customOrganic layer was dried
  9. customevaporated

Sources & evidence

ORD record
ord-e932ce18811346da8447086651ab00ce
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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